Cyhalothrin is a colorless solid. Insoluble in water. Used as a wide spectrum insecticide.
颜色/状态：
Viscous liquid yellow-brown
气味：
Mild
蒸汽压力：
1.1X10-6 mm Hg at 25 °C (est)
稳定性/保质期：
Stable to decomp & cis-trans isomerization for at least 4 yr in the dark at 50 °C. Stable to light; loss on storage in the light is < 10% in 20 months. Decomposes at 275 °C. Slowly hydrolyzed by water in sunlight at pH 7-9, more rapidly at pH >9.
Major metabolic reactions are ester hydrolysis and hydroxylation at the alcohol moiety. The metabolic fates of the alcohol moiety, alpha-cyano-3-phenoxybenzyl alcohol, was the same as those of pyrethroid insecticides having the same alcohol moiety. ... The cyano group of the alcohol moiety of cyhalothrin is expected to undergo conversion to SCN ion. The major metabolites of the acid moiety are cyclopropylcarboxylic acid and its glucuronide and those from the alcohol moiety is PBacid, 4'-OH-PBacid and sulfate of 4'pOH-PBacid.
The comparative metabolism of gamma-cyhalothrin with or without enantiomer pari A and cyhalothrin revealed that enantiomer pair A had little or no effect on the absorption, distribution, tissue retention, or metabolic profiles, implying that enantiomers of cyhalothrin behave independently.
In common with other structurally related pyrethroids, the main routes of metabolism of cyhalothrin in the cow have been found to be similar to those observed in rats and dogs, i.e cleavage of the ester bond with subsequent excretion of the cyclopropyl carboxylic moiety, either free, hydroxylated, or as a glucuronide conjugate. The phenoxybenzyl moiety was further metabolized by loss of the nitrile group and excreted as free 3-phenoxybenzoic acid and its amino acid conjugate, or after aromatic hydroxylation probably at the 4'position. Cyhalothrin itself gives rise to residues in fats; this is consistent with lipophilic properties of cyhalothrin compared to those of its more polar metabolites.
Identification of the metabolites produced in the rat studies revealed that, following oral administration, unabsorbed cyhalothrin was eliminated unchanged via the feces. The absorbed material was rapidly and extensively metabolized and no unchanged cyhalothrin was present in urine or bile. The main route of metabolism was, as anticipated, via hydrolysis of the ester linkage. The cyclopropanecarboxylic acid moiety was subsequently excreted via the urine as the glucuronide conjugate. This material accounted for about 50% of the radioactivity in urine following dosing with (14)C-cyclopropyl-labelled cyhalothrin. The 3-phenoxybenzyl moiety was further metabolized by loss of the nitrile group, oxidation of the aldehyde formed to a carboxylic acid, aromatic hydroxylation at the 4'-position, and formation of the 4-O-sulfate conjugate of 3-(4-hydroxyphenoxy)benzoic acid. This conjugate accounted for approximately 75% of the urinary radioactivity following dosing with (14)C-benzyl-labelled cyhalothrin. No metabolite containing the ester function was detected.
Cyhalothrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. The main route of metabolism is, as anticipated, via hydrolysis of the ester linkage. The cyclopropane-carboxylic acid moiety is subsequently excreted via the urine as the glucuronide conjugate. The 3-phenoxybenzyl moiety is further metabolized by loss of the nitrile group, oxidation of the aldehyde form to a carboxylic acid, aromatic hydroxylation at the 4' position, and formation of the 4- O-sulfate conjugate of 3-(4-hydroxyphenoxy)benzoic acid. (L871)
Metabolic studies have been carried out on /various mammalian species/. In rats and dogs, cyhalothrin has been shown to be well absorbed after oral administration, extensively metabolized, and eliminated as polar conjugates in urine. ... Residues in rats were eliminated with a half-life of 23 days. ... In all mammalian species investigated, cyhalothrin has been found to be extensively metabolized as a result of ester cleavage to the cyclopropanecarboxylic acid and 3-phenoxybenzoic acid, and eliminated as conjugates. In fish, the main residue in tissues consists of unchanged cyhalothrin, and there are lower levels of the ester cleavage products. Under laboratory conditions of constant toxicant concentrations, cyhalothrin and lambda-cyhalothrin are highly toxic to fish and to aquatic invertebrates. ... Accumulation studies conducted under laboratory conditions with constant concentration show that rapid uptake takes place in fish ... Since the compound is rapidly absorbed and degraded under natural conditions, there will not be any practical problems concerning the accumulation of residues or the toxicity of cyhalothrin or lambda-cyhalothrin in aquatic species. Cyhalothrin and lambda-cyhalothrin are virtually non-toxic to birds ... Under laboratory conditions, cyhalothrin and lambda-cyhalothrin are toxic to honey bees ... However, in the field the hazard is lower ... Cyhalothrin and lambda-cyhalothrin are type II pyrethroids; clinical signs /of toxicity/ include ataxia, unsteady gait, and hyperexcitability. In the rabbit, cyhalothrin is a moderate eye irritant and lambda-cyhalothrin is a mild eye irritant; both are mild skin irritants. /Cyhalothrin/ is a moderate skin sensitizer in the guinea pig. Lambda-cyhalothrin is not a skin sensitizer. ... Cyhalothrin and lambda-cyhalothrin gave negative results in a range of in vivo and in vitro assays designed to detect gene mutations, chromosomal damage, and other genotoxic effects. When orally administered to the rat and rabbit during the period of major organogenesis, cyhalothrin was neither embryotoxic or teratogenic at dose levels that elicited maternal toxicity ... In manufacturing, formulation, laboratory work and field usage, /human/ symptoms of subjective facial sensation have been reported. ... Subjective facial skin sensations, which may be experienced by people who handle cyhalothrin and lambda-cyhalothrin are believed to be brought about by repetitive firing of sensory nerve terminals in the skin. They may be considered as an early warning signal indicating that overexposure of the skin has occurred. ... The exposure of the general population to cyhalothrin and lambda-cyhalothrin is expected to be very low and is not likely to present a hazard under recommended conditions of use. ... Cyhalothrin and lambda-cyhalothrin are unlikely to present a hazard to those occupationally exposed. ... Under laboratory conditions cyhalothrin and lambda-cyhalothrin are highly toxic to fish, aquatic arthropods, and honey bees. However, under field conditions, lasting adverse effects are not likely to occur under recommended conditions of use.
Both type I and type II pyrethroids exert their effect by prolonging the open phase of the sodium channel gates when a nerve cell is excited. They appear to bind to the membrane lipid phase in the immediate vicinity of the sodium channel, thus modifying the channel kinetics. This blocks the closing of the sodium gates in the nerves, and thus prolongs the return of the membrane potential to its resting state. The repetitive (sensory, motor) neuronal discharge and a prolonged negative afterpotential produces effects quite similar to those produced by DDT, leading to hyperactivity of the nervous system which can result in paralysis and/or death. Other mechanisms of action of pyrethroids include antagonism of gamma-aminobutyric acid (GABA)-mediated inhibition, modulation of nicotinic cholinergic transmission, enhancement of noradrenaline release, and actions on calcium ions. They also inhibit calium channels and Ca2+, Mg2+-ATPase. (T10, T18, L857)
来源:Toxin and Toxin Target Database (T3DB)
毒理性
致癌性证据
癌症分类：D组 不可归入人类致癌性类别
Cancer Classification: Group D Not Classifiable as to Human Carcinogenicity
来源:Hazardous Substances Data Bank (HSDB)
毒理性
致癌物分类
对人类不具有致癌性（未被国际癌症研究机构IARC列名）。
No indication of carcinogenicity to humans (not listed by IARC).
At high doses, signs of poisoning attributable to cyhalothrin include profuse salivation and pulmonary edema, clonic seizures, opisthotonos (i.e., the spine is bent forward such that a supine body rests on its head and heels), coma, and death. At lower doses, commonly observed effects include paresthesia and erythema. (L863)
来源:Toxin and Toxin Target Database (T3DB)
吸收、分配和排泄
在大鼠中，口服给药后，氯菊酯会迅速通过尿液和粪便排出体外。酯基团被水解，两个部分都形成极性共轭物。
In rats, following oral admin, cyhalothrin is rapidly eliminated in urine & feces. The ester group is hydrolyzed, both moieties forming polar conjugates.
After twice daily oral ingestion of (14)C-benzyl- or (14)C-cyclopropyl-labelled cyhalothrin (1 mg/kg/day for 7 days), absorption of the insecticide by cows was apparently slow and incomplete. Approximately 50% of the dosed radioactivity was excreted in the feces, mainly as unchanged cyhalothrin, but only small amounts were detected in the bile. With both labelled forms, most of the radioactive material was rapidly eliminated in the urine (27%) and feces (49%) within 24 hr of each daily dose. Only a very small proportion of the dose was secreted in the milk (0.8%) and this was found to be unchanged cyhalothrin. Tissue residues of radioactive material were low and were in the following order: fats> liver> blood> muscle. Residues in fat consisted of unchanged cyhalothrin. The liver and kidney contained small amounts of cyhalothrin, but the residues were largely due to a number of ester-cleavage metabolites that were probably present because the animals were still actively metabolizing and eliminating a significant fraction of the most recent day's intake of cyhalothrin. The almost two-fold difference in the plasma levels of total radiolabelled components obtained with the different labelled forms suggests that little cyhalothrin was present in blood. The ester link must therefore be hydrolysed very rapidly, apart from a small fraction that is distributed into fatty tissues.
The absorption,distribution, excretion, and metabolism of cyhalothrin have been studied in the dog using cyhalothrin labelled either in the acid (14)C-cyclopropyl or alcohol (14)C-benzyl moieties of the molecule. Groups of three male and three female beagle dogs were given a single oral dose of cyhalothrin (1 mg/kg or 10 mg/kg) and, after a 3-week interval, a further single intravenous administration of 0.1 mg/kg. Samples of blood and excreta were collected for 7 days after dosing and were analysed for total radioactivity. The proportions of unchanged cyhalothrin and of metabolites in urine and feces were determined by thin-layer chromatography. The identity of major metabolites was confirmed by mass spectrometry. The absorption of cyhalothrin after oral administration was variable. The degree of absorption was difficult to assess but was within the range 48%-80%. Excretion of radioactivity after both oral and intravenous dosing was initially rapid, with most of the administered radioactivity being excreted in the first 48 hr after dosing. After 7 days, a mean of 82-93% had been excreted.
Groups of six male and six female Alderly Park rats received a single oral dose (1 or 25 mg/kg) of radiolabelled cyhalothrin in corn oil. As it was known that the metabolism of related pyrethroids involves extensive cleavage of the ester bond, duplicate experiments were performed using two forms of cyhalothrin labelled with (14)C in the acid (14)C-cyclopropyl or alcohol (14C-benzyl) portions of the ester. ... Following oral administration of cyhalothrin, absorption was variable but accounted for about 55% of the dose. The proportions absorbed were similar at both dose levels. Excretion was rapid for both (14)C-cyclopropyl- and (14)C-benzyl- labelled cyhalothrin at both dose levels, although excretion rates were faster with the (14)C-benzyl label than with the (14)C-cyclopropyl label. Urinary excretion accounted for approximately 20-40% of the dose and fecal excretion for 40-65% of the dose during the first 7 days. Peak blood concentrations of radioactivity were reached within 4-7 hr, and by 48 hr these concentrations had declined to 10% or less of peak values. A small proportion of an oral dose (2-3%) was retained in the animals after seven days; analysis of twelve different tissues indicated that this radioactivity was present mainly in white fat.
[EN] ACC INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE L'ACC ET UTILISATIONS ASSOCIÉES
申请人：GILEAD APOLLO LLC
公开号：WO2017075056A1
公开（公告）日：2017-05-04
The present invention provides compounds I and II useful as inhibitors of Acetyl CoA Carboxylase (ACC), compositions thereof, and methods of using the same.
[EN] BICYCLYL-SUBSTITUTED ISOTHIAZOLINE COMPOUNDS<br/>[FR] COMPOSÉS ISOTHIAZOLINE SUBSTITUÉS PAR UN BICYCLYLE
申请人：BASF SE
公开号：WO2014206910A1
公开（公告）日：2014-12-31
The present invention relates to bicyclyl-substituted isothiazoline compounds of formula (I) wherein the variables are as defined in the claims and description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
The present invention relates to azoline compounds of formula (I) wherein A, B1, B2, B3, G1, G2, X1, R1, R3a, R3b, Rg1 and Rg2 are as defined in the claims and the description. The compounds are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to a method for controlling invertebrate pests by using these compounds and to plant propagation material and to an agricultural and a veterinary composition comprising said compounds.
